What are tautomers? What applications do they have in modern chemistry?

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What are tautomers? What applications do they have in modern chemistry?

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Answer 1 · 2016-04-10T09:40:37

Tautomers are constitutional isomers, that readily interconvert. The classic tautomerism is keto-enol tautomerism, which I will illustrate.

Explanation:

A ketone, for instance, acetone, has a enol tautomer:

$H_{3} C - C (= O) C H_{3} ⇌ H_{2} C = C (- O H) C H_{3}$ $H_3C-C(=O)CH_3 rightleftharpoons H_2C=C(-OH)CH_3$

These are clearly constitutional isomers as they each have the same $C_{3} H_{6} O$ $C_3H_6O$ formula, but the equilibrium strongly lies to the left. With other diketones, for instance acetylacetone, the equilibrium lies more to the right.

As to the applications, such enol tautomerism allows for $C - C$ $C-C$ bond formation, as the enol hydrogen is acidic, and can be deprotonated to give $H_{2} C = C (- O^{-}) C H_{3}$ $H_2C=C(-O^-)CH_3$ , the enolate. The negative charge can be delocalized onto the carbon centre (i.e. as $H_{2}^{-} C - C (= O) C H_{3}$ $H_2^(-)C-C(=O)CH_3$ ), the carbanion, and $C - C$ $C-C$ bond formation can be accomplished.

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What are tautomers? What applications do they have in modern chemistry?

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